Polycyclic ethers and an unexpected dearomatisation reaction during studies towards the bioactive alkaloid, perophoramidine

Add time:09/10/2019    Source:sciencedirect.com

The bioactive alkaloid natural product perophoramidine and the related family of compounds known as the communesins have inspired the synthesis community for more than a decade. Many of the elegant approaches have required the synthesis of complex intermediates that have not always reacted in the expected manner. In this study we describe a series of cyclic ether-containing precursors that were prepared during our synthetic studies towards these natural products. Attempts to open the cyclic ether ring and trap the resulting stabilised carbocation with a carbon nucleophile ultimately led to the preparation of a diallyl-substituted all carbon quaternary centre. Subsequent attempts to differentiate between the two allyl groups resulted in a relatively clean transformation to an unexpected compound. Extensive structural characterisation, including small molecule X-ray crystallography, showed that a dearomatisation reaction had occurred.

We also recommend Trading Suppliers and Manufacturers of IODOMETHYL METHYL ETHER (cas 13057-19-7). Pls Click Website Link as below: cas 13057-19-7 suppliers

Prev:Regular ArticleMicrowave Spectrum, Structure, and Nuclear Quadrupole Coupling Constant Tensor of IODOMETHYL METHYL ETHER (cas 13057-19-7)
Next:[2,3]-Wittig rearrangements of (trimethylsilyl)methyl allyl ethers)